Homestead on the Roof

4.5

749 Reviews

$50 and over

Portuguese

Make a booking

2 people

24 Dec 2024

23:00

Charming
Neighbourhood gem
Great for outdoor dining

Homestead On The Roof— our cozy rooftop restaurant— is tucked away above Roots Handmade Pizza in the heart of West Town & features a farm-fresh Portuguese-influenced menu from Chef Christopher Teixeira.

The warm & cozy interior features a seasonally rotating tasting menu, which incorporates ingredients from our own farm and local vendors into our nationally recognized cuisine.

The magic of Homestead is its 85-seat outdoor rooftop patio with a full view of the L-shaped, 3,000-square-foot organic rooftop garden, two massive, vertical hanging gardens, dozens of planter boxes full of fruits, veggies, and herbs, and a fireplace.

Private dining

Book your next event with us

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Additional information

Dining style
Casual Elegant
Price
$50 and over
Cuisines
Portuguese, Farm-to-table, Contemporary European
Hours of Operation
Thu–Sat 5:00 pm–11:00 pm Dinner Wed, Sun 5:00 pm–9:00 pm
Phone number
(773) 332-2354
Website
http://www.homesteadontheroof.com/
Payment Options
AMEX, Discover, Mastercard, Visa
Dress code
Smart Casual
Executive Chef
Chris Teixeira
Catering
Homestead on the Roof does have the capabilities to cater outside events and venues. Please email events@homesteadparties.com
Private party facilities
One of the city's best rooftops with a garden, cobblestone fireplace, rustic candlelit chandelier, & vine-climbing pergola, Homestead is a premier year round destination for your most special events and corporate buyouts.
Private party contact
Jena Cherry: (773) 904-1149

Location
1924 W Chicago Ave, Chicago, IL 60622
Area
West Town
Cross Street
Winchester (entrance through ROOTS HANDMADE PIZZA)<br />
Parking details
Metered parking available all along Chicago Avenue & Winchester.
Public transit
Damen Ave "50" CTA bus. Chicago Ave "66" CTA bus.
Entertainment
None
Additional
Patio/Outdoor Dining

What 749 people are saying

Overall ratings and reviews

Reviews can only be made by diners who have eaten at this restaurant

4.5

4.5 based on recent ratings

4.6Food
4.1Service
4.7Ambience
4.4Value

Noise • Moderate

Review summary

AI-generated from verified diner reviews

Homestead on the Roof is a charming rooftop retreat in West Town, celebrated for its "beautiful but unpretentious" atmosphere and "high quality, high value" touches. Diners rave about the "fabulous" food and "delicious" cocktails, making it an ideal spot for date nights. While service can be slow during busy times, the overall experience is positive, with many guests eager to return.

749 Reviews

J
Jen
Chicago
2 reviews
5.0
2 reviews
Dined on 25 September 2024
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 5
Outstanding all around, a Wonderful hidden gem! Love this place.
Is this helpful?
OT
OpenTable Diner
Detroit
1 review
5.0
1 review
Dined on 20 September 2024
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 5
Awesome experience, friendly waiter Nigel was great. Food was stellar. Place was a little hard to find but overall excellent evening with them.
Is this helpful?
A
Amanda
Chicago
7 reviews
5.0
7 reviews
Dined on 16 September 2024
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 5
Food is wonderful (we shared the whole duck dinner) and the rooftop garden is such a beautiful place to eat on a perfect Chicago evening.
Is this helpful?
M
Matt
Austin
1 review
5.0
1 review
Dined on 15 September 2024
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 4
Awesome secret spot with fantastic Portuguese cuisine.
Is this helpful?
M
Michelle
Minneapolis
2 reviews
1.0
2 reviews
Dined on 14 September 2024
1. Overall 1
2. Food 2
3. Service 1
4. Ambience 4
We got seated 35 minutes after our reservation time, our server was barely attentive and had poor table side manner and food was pretty mediocre especially for the price. Overall, disappointed.
Is this helpful?
N
Nicholas
VIP
San Francisco
5 reviews
4.0
5 reviews
Dined on 2 September 2024
1. Overall 4
2. Food 4
3. Service 1
4. Ambience 4
Food was great. Service was very slow at a half full restaurant. Also the table that sat down after us was served before us.
Is this helpful?
G
Gloria
VIP
Chicago
10 reviews
2.0
10 reviews
Dined on 25 August 2024
1. Overall 2
2. Food 3
3. Service 1
4. Ambience 3
I would not suggest dining here. The roof top was ok but the service was very poor and food just ok. The server apologized that they were understaffed but that didn’t compensate for not getting our drinks timely, trying to understand the wine selection and food preparation. Sad to say take this one off your list
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E
Eric
Chicago
1 review
4.0
1 review
Dined on 24 August 2024
1. Overall 4
2. Food 4
3. Service 4
4. Ambience 5
Duck fried rice a bit salty for my liking but otherwise great food and ambience
Is this helpful?
C
Chrisy
Chicago
5 reviews
5.0
5 reviews
Dined on 23 August 2024
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 5
Lovely experience all around! Excellent menu and presentation- enjoyed the octopus, scallops and short rib in particular, but everyone was exceptional. Cocktails, service and ambience perfect setting both for group or date night. Great music too- highly recommend
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J
Jeffrey D
Los Angeles
7 reviews
5.0
7 reviews
Dined on 21 August 2024
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 5
Dinner was wonderful and the staff was really friendly!
Is this helpful?

FAQs

Homestead on the Roof is rated 4.5 stars by 749 OpenTable diners.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable.

Make a booking

2 people

24 Dec 2024

23:00

1924 W Chicago Ave, Chicago, IL 60622

Additional information

Cross Street
Winchester (entrance through ROOTS HANDMADE PIZZA)<br />
Area
West Town
Hours of Operation
Thu–Sat 5:00 pm–11:00 pm Dinner Wed, Sun 5:00 pm–9:00 pm
Price
$50 and over
Cuisines
Portuguese, Farm-to-table, Contemporary European
Dining style
Casual Elegant
Dress code
Smart Casual
Parking details
Metered parking available all along Chicago Avenue & Winchester.
Public transit
Damen Ave "50" CTA bus. Chicago Ave "66" CTA bus.
Payment Options
AMEX, Discover, Mastercard, Visa
Executive Chef
Chris Teixeira
Entertainment
None
Additional
Patio/Outdoor Dining

Website
http://www.homesteadontheroof.com/
Phone number
(773) 332-2354
Catering
Homestead on the Roof does have the capabilities to cater outside events and venues. Please email events@homesteadparties.com
Private party facilities
One of the city's best rooftops with a garden, cobblestone fireplace, rustic candlelit chandelier, & vine-climbing pergola, Homestead is a premier year round destination for your most special events and corporate buyouts.
Private party contact
Jena Cherry: (773) 904-1149

Homestead on the Roof

Make a booking

Private dining

Additional information

Menu

What 749 people are saying

Overall ratings and reviews

Review summary

FAQs

How is Homestead on the Roof restaurant rated?

Is Homestead on the Roof currently accepting bookings?

Make a booking

Additional information